Potassium Iodide → [2-(3-Cyano-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

HRID 1785425Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C-:19]#[N:20].[Na+].[I-].[K+]>[Cu](I)I.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:19]#[N:20])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

To a sealed pressure tube was added [2-(3-bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.23 g, 3.9 mmol), sodium cyanide (250 mg, 5.1 mmol), potassium iodide (130 mg, 0.8 mmol), N-N′-dimethylethylenediamine (0.41 mL, 3.9 mmol), and toluene (6 mL). This suspension was then sparged with nitrogen prior to adding copper iodide (150 mg, 0.8 mmol). Reaction mixture heated to 130° C. for 16 h while stirring. Reaction partitioned between ethyl acetate and 30% aqueous ammonia. Organic washed with saturated ammonium chloride, then dried over magnesium sulfate. Reaction reduced to an oil under vacuum and isolated as a white solid after purification on silica. M+1=261.

Workup

customThis suspension was then sparged with nitrogen
customReaction mixture
customReaction
custompartitioned between ethyl acetate and 30% aqueous ammonia
washOrganic washed with saturated ammonium chloride
dry with materialdried over magnesium sulfate
customReaction
customisolated as a white solid
customafter purification on silica

Sources & evidence

ORD record: ord-95b831007d3a45b8a724f5ec6009c0d9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504403B2

Reaction notes

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